To bootstrap, you need funds. To gain funds without investors, you need to save. One of the best ways to do that is to practice ERE. So there is an interesting tie in there.
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I think we need more people starting viable businesses that solve problems the Silicon Valley bubble doesn't even see.

I like this line of thinking, as I've had similar thoughts myself. And I agree that there are some glaring problems out there that can be solved with software, but they aren't being tackled due to blind spots created by the typical SV viewpoint.

I have a lot I want to do before my dream job. I want to finish bootstrapping at least one company to the point it could support me full time.
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But all that is an awful lot of work. Maybe.

Maybe no need to start a company right away? Perhaps an open source project. Write some software in the open -- with no prospect of making money -- and see if it can be useful to others. If it is, you're the best person to provide support. This is a tried-and-true path: MySQL, MongoDB, nginx, etc.

@Chris Oh, I meant a lot of work to do the whole dream job of bootstrapping a bootstrapping community.

I'm already bootstrapping a company outside of my day job. I've been working on it for ~1.5 years now with a friend. I officially incorporated it a month ago so we could start depositing the backlog of checks from our lone customer. A rough ballpark is we need 40 customers we'll be doing really well (as in, could both do it full time w/ me having the same salary and him getting a huge raise). So we have to figure out customer acquisition. The good news is we know exactly who our customers are (like the actual people by name -- not segments). We "just" have to get good at selling to them. We can't risk turning them off so we have to tread carefully while we figure it out. We took on kind of a big project though so it's taken awhile to get the product to the point that it is useful and solving problems in a more efficient way for our target market than most other solutions. We have a potential customer waiting on a feature I'm working on now so hopefully, we can deliver what they want and get to 2/40th of the way .

I've done the open source thing for a tool we needed at a job a couple startups ago. It was fun to see it grow. Over 700,000 downloads on rubygems! I've done some other smaller open source things too. It's definitely enjoyable. My current focus is single page applications with React so my stack for our startup is nginx, PostgreSQL, Redis, React, NodeJS with Koa (at first, I was just going to prototype with it but I actually love it with async await), some server-side queues, some AWS services (S3, CloudFront, SES) and Twilio (SMS). It's pretty amazing paying about 40 cents a month for AWS and getting all this value (server is hosted elsewhere for now, I might go for elastic beanstalk and more AWS services once it's a minor cost).

But really just not having to work would be great. I think part of what makes a job, any job, unpleasant is the shackles it places upon you. The obligation to do it day in and day out every day according to regimented times and to always be doing the same thing. I think that can make any type of job, including wildlife photographer, less enjoyable.

I think having the freedom to dabble here and there in a variety of different things when I want on a consultancy basis would be my cup of tea.

But, I do want to volunteer as labor, in a variety of fields. Stone masonry would top the list. Lots of things can be learned in a book, or a video, some things must be learned by doing. I can mix mortar, and stack rocks, and in fact have. But there's nothing like having someone pick apart your work as you do it to improve how you do it.

So for me, I'll be using my labor to pay professionals to improve my skills in areas I want to develop. But that's hardly a job. Internship, that's what I am thinking about. I don't want to apprentice, I doubt my interest will last that long. But 2-3 weeks hauling rocks is likely to teach me everything I want to know about it.

Each time this comes up, author is a popular choice. Not for me, but for those who are interested, Scott Alexander, from slate star codex wrote and published a book, unsong, athttp://unsongbook.com

The book was very good, but I really liked the way he did the editing and publishing. I feel like ebooks are an adaptation of an old publishing model using new tech. This is more of an organic, fresh approach to the concept of publishing in an age of information.